53939-27-8Relevant articles and documents
Tumlinson et al.
, p. 203,210 (1975)
(E4,Z9)-Tetradecadienal, a sex pheromone for three North American moth species in the genus Saturnia
Mcelfresh, J. Steven,Millar, Jocelyn G.,Rubinoff, Daniel
, p. 791 - 806 (2007/10/03)
The lepidopteran genus Saturnia has three representatives in North America, S. walterorum, S. mendocino, and S. albofasciata. (E4,Z9)-Tetradecadienal (E4,Z9-14:Aid) was identified as a sex pheromone component for all three species by combinations of coupled gas chromatography-electroantennogram detection (GC-EAD), GC-mass spectrometry (MS), and field trials. In field trials, all three species were strongly attracted to (E4,Z9-14:Ald) as a single component, Small amounts of (Z)-9-tetradecenal (Z9-14:Ald) also were found in extracts of all three species, but blends of this compound with E4,Z9-14:Aid were no more attractive to male moths than E4,Z9-14:Ald alone. Extracts of pheromone glands of female S. walterorum occasionally contained a third, trace compound eliciting responses from male antennae in GC-EAD experiments, but this compound was not identified. It is suggested that the three species can use the same, single component as a sex attractant because the flight period of S. albofasciata (fall) is different than that of the other two species (spring), whereas the geographic distributions of S. mendocino and S. walterorum overlap over only small portions of their ranges. Furthermore, the latter two species readily hybridize, so there may be minimal fitness cost to cross-attraction.
Metamorphosis of Castor Oil to Insect Sex-pheromones and Useful Synthons
Ranganathan, S.,Maniktala, Vibha,Kumar, Raaj,Singh, G. P.
, p. 1197 - 1207 (2007/10/02)
The primary fragmentation products of Castor oil (1), namely, methyl undec-10-enoate (2) and sebacic acid (3) have been converted, using novel reactions and strategies into synthons of the type H-CC-(CH2)n-3-CH2OTHP (n=6=4; n=7=14; n=8=22; n=9=29).A surprisingly clean decarboxylative elimination of sebacic acid monoester gives methyl non-8-enoate (7), a synthon related to recefeiolide and a precursor to 4, the utility of which, has been illustrated with the synthesis of insect-pheromones of the species Grapholita molesta.Methyl dec-9-enoate (15) has been prepared by a novel and practical terminal ? to lower terminal ? degradation of 2.Compound 7 has been transformed via synthon 14 to the insect sex-pheromones of the species, Spodoptera frugiperda, Heliothis virescens and Paralobesia viteana in high yields and excellent stereochemical purity. 1-Tetrahydropyranyloxyundec-10-yne (22) readily prepared from 2, has been used to illustrate a new strategy in pheromone synthesis, namely, the use of coupling elements, leading to the preparation of bombykol in high yields and excellent stereochemical purity. 1-Tetrahydropyranyloxydodec-11-yne (29), already reported, has been transformed to vaccenic acid (30), the transposed ?-isomer of oleic acid, in good yields, thus demonstrating the use of acetylide synthons for the preparation of rare fatty acids also.
